


I'm In Love With You, Jack! Or (How To Confess Your Love To Your Best Friend Of Almost Thirty Years Or Die Trying.)

by solversonlou



Category: Will & Grace
Genre: Feelings Realization, Friends to Lovers, Gay Male Character, Love Confessions, M/M, Male-Female Friendship, Mutual Pining, pop culture references
Language: English
Status: Completed
Published: 2017-12-29
Updated: 2017-12-29
Packaged: 2019-02-23 13:20:42
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,013
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13190967
Author URL: https://archiveofourown.org/users/solversonlou/pseuds/solversonlou
Summary: It's not like he has to tell Jack how he feels tonight, or any night for that matter. It's been years of friendship with nothing between them. Why ruin it?Will realises he's in love with Jack and tries to figure out how to tell him.





	I'm In Love With You, Jack! Or (How To Confess Your Love To Your Best Friend Of Almost Thirty Years Or Die Trying.)

"You didn't call him back? But he was perfect for you. He was boring, bland..." Jack rolls his eyes then moves into his robot impression pose, voice monotone as he speaks. "Bleep bloop, I am Will Truman bot, I do not feel human emotions."

"Jack, I know this may be hard for you to believe, but I am actually capable of feeling things," Will says, brows drawn together in frustration at Jack's insistence on treating everything as a joke.

"Oh, Will, I know that," Jack waves a hand dismissively at Will's seriousness. He chuckles, hops onto Will's couch _slumber party style_ and grins up at him. "I'm just joshing with ya! Why'd you invite me over anyway? Ooh, Are we gonna watch _Carol_ again and complain about how the Oscars snubbed Cate Blanchett?"

"No, Jack, I didn't invite you to watch--" Will pauses, hand held out in a stopping motion as he backtracks. His head tilts to the side as he speaks. "You know, I'm not a big fan of Blanchett. I think people just like her because she's tall."

"How dare you!" Jack gasps, clutching at his chest like an old lady grabbing at her pearls. "Cate Blanchett is an American hero."

"She's Australian, Jack," Will deadpans, shaking his head. 

A long, defeated sigh leaves Will as he crosses the room, pinching the bridge of his nose as he wonders to himself why he's doing this in the first place. It's not like he _has_ to tell Jack how he feels tonight, or any night for that matter. It's been years of friendship with nothing between them. Why ruin it? 

He's overthinking again, something he scolds himself for as he takes in a long breath and sits down in the couch besides a concerned looking Jack.

"What's with all the huffing and blowing?" Jack gestures in the space around Will with his hand. "Oh, you're not having a panic attack, are you? Here, breathe into Grace's purse."

Will blinks open his eyes, brow furrowed at the faux leather handbag extended out to him. He pushes it away, "It's a paper bag for a panic attack... which I'm not having, by the way."

Jack flutters his lashes, intrigued as he carelessly tosses Grace's purse behind him and tilts his head, interested in Will's predicament.

"I just..." Will purses his lips, looks at the floor then back up at Jack, then at the floor and back again, words churning over in his head, rehearsed and ready. Stomach twisting, he can feel the pinprick tingles in his palms as he slides them over his thighs, fidgeting like a school kid before a presentation. "I have something I need to tell you, and I don't really know how to tell you, or if I should tell you."

"Ooh, if it's about me, I have to know," Jack's eyes widen, fingers clasping Will's forearm, squeezing tight. "I can't _not_ know any gossip on me, what are the kids saying these days?"

Will blinks again, slowly, mouth agape as if to search for words, "Why on earth would _'the kids'_ be talking about you?"

"I don't know," Jack says, mimicking brushing imaginary hair over his shoulders, a sly grin on his face. "Maybe they know about my latest one man show."

"Oh, Jack," Will can't help but smirk, patting Jack's knee. "Streaming yourself eating copious amounts of food online to lonely Korean men isn't a one man show."

Jack slaps Will on the leg, playful but annoyed, "It's called _Mukbang_ , and it's an art form."

Will chuckles softly, chest swimming with warmth as he bows his head. His smile fades as the anxiety returns, bubbling away in his stomach. He swallows, scratching the back of his neck.

Jack's eyes are soft when Will looks back up at him, and Will swallows again, trying to remember the speech rehearsed in his head, but the lines are jumbled up and he can't seem to get any of them out.

"Will, what's wrong?" Jack's feet plant on the floor as he twists towards Will, placing a hand on the other man's knee. "You're not sick, are you?"

Will looks down at the fingers on his knee, his own fingers itching to take them. If only he could look Jack in the eye and say it. _'I'm in love with you, Jack.'_

"No," Will says, forcing a smile to mask his nerves. He looks up at Jack, _sweet, naive, annoying, yet lovable Jack._ Strong, brave, funny Jack. _His best friend Jack._

Will's stomach drops as he pats him on the knee again, clearing his throat, "I'm fine, it's just... Grace. You, uh, you know that grocery store clerk you were into, well turns out he's straight and Grace got his number."

"That harpy!" Jack slaps Will's knee hard, turning away from him in shock. "This is what Dolly must have felt like when she wrote _Jolene_!"

Will winces at the sting from the slap, rubbing his knee as he laughs, chest suddenly feeling empty. _Well done, Truman, you blew it._ "Maybe so... but I somehow doubt Dolly's guy was a vegan hipster with a mountain man beard."

\- - -

"Maybe I shouldn't tell him," Will says, sitting in Grace's office on her desk, eating from a takeout box of salad. "I mean, why ruin our friendship with feelings? We're fine the way we are."

"Will, we dated and we're still friends," Grace reasons, standing at the fold out table with her design plans laid out on it. "Feelings can only ruin a friendship if you let them, and besides, who better to fall in love with than your best friend?"

Will shifts, considering Grace's words, "But you and I were different. For one, Jack and I are both gay."

"So?" Grace looks up, gestures with her hand as she speaks. "I had feelings for you, you didn't return them. If Jack doesn't return your feelings, then I'm sure you two can recover. You'll move on like I did. And if not, hey, you can always find a new gay best friend you won't fall in love with. How's Karen's Beverly doing these days?"

Will rolls his eyes at the last part, shaking his head as Grace snorts out a laugh, "Grace, your point is made redundant when you joke like that."

Grace sighs, walks over from her table to Will, places her hands on his arms and rubs them gently, "Look, you either gotta be brave or trust what you think is right. I know Jack can seem like he doesn't take things seriously, but he's understanding when he needs to be. I'm sure he'll understand."

Will exhales, drops his head before nodding slowly and looking back up at Grace, "Thank you, Gracie, you really helped me out."

Grace kisses his forehead, "I always do." 

\- - -

Jack's forty-eighth birthday is held in Will's apartment for reasons beyond his grasp. 

Jack had insisted it was because his place was being remodelled, but Will knew he didn't have the funds to support that. He figures the apartment is just a tip from whatever group of twinks Jack had brought home from the bar last night and he just can't be bothered to clean up.

Karen arrives with a bottle of gin that she drinks all by herself, and most of the party consists of Jack being centre of attention, talking to every guest that isn't Will. 

Will doesn't blame him at all. After all, it _is_ his party, and besides, Will has been spending most of the evening wondering how to get Jack alone so he can tell him how he feels.

It's after the stripper dressed as _Pennywise the clown_ , (a character Jack had expressed a weird attraction to), has finished his performance, that Will retires to the balcony, leaning against the brick divider as he looks out onto the city.

His head is swimming again, weighing out the outcomes of his potential confession.

"Hey," a voice breaks Will out of his thoughts, draws his attention to turn around. Jack appears around the sliding doors, the sound of a dying down party muffled behind him as he closes them. "Room for a little one?"

Will smiles, waves him over, "I don't know if forty-eight is considered little, but go ahead."

Jack scoffs as he walks over, leans against the brick and looks out onto the lights of the city.

It's silent between them for a moment, the cool air rising goosebumps on their skin as they take in the scenery, the sound of cars beeping below them in the New York streets.

Will had expected a comeback from Jack, but he supposes he's in a good enough mood not to give him one. 

Instead, Jack breaks the silence and speaks, voice soft, "Lotta things have happened on this balcony."

"Like what, exactly?" Will implores, looking towards Jack who's looking up at the stars, a twinkle in his eye. Will swallows, nervous again.

"Remember when you helped me come out to my mom?" Jack turns his head, looks at Will with a fond smile on his features. "You stood here and told me how much I helped you in college to come out, and it was all the courage I needed. Me helping you be brave, helped me be brave."

Will's chest blooms at the memory, his lips curling up into a smile as he remembers standing on the very same balcony, in the year two thousand, seventeen years ago. It's been so long, Will can hardly believe it, "You've always been there for me, Jack. It's only fair that I'm there for you too."

Jack's fingers flex over the brick, his face turning back towards the city as he smiles, "Thank you."

"For the party?" Will asks, pointing with his thumb behind him. "Because that was mostly Ricardo, the party planner from my gym."

Jack chuckles, looks down at his hands on the wall, "Well, thank you for that, too. But also... for everything. You've always been there for me, as well. Even if I _can_ be a bitch sometimes, and you can be a jerk. I'll always care about you, Will, and I'll always love you."

Will's throat tightens at those words. _Love._ How many definitions can one word have? How do you measure it? Lyrics from _Rent_ ring in his head.

"I'll always care about you too, Jack," Will manages to get out, face warm despite the cold air as Jack turns towards him, arms moving to pull him into a hug. His hands fit against Jack's back almost immediately, like they did all those years ago, like they've done a hundred times before. He inhales sharply, eyes sliding shut as Jack's cologne hits him, a warm familiarity that settles in. He murmurs, lips pressed to Jack's shoulder. "I love you too."

They stay like that for a moment, Will churning over the weight and implications of his word. He's said them, but what do they mean? _Does Jack know?_

Jack is the first one to pull away, and the lack of weight against Will leaves him feeling empty, yearning for more. 

Jack smiles at him, sweet and soft, and Will's stomach drops. _He doesn't get it, does he?_

"Well, we better get back before Karen starts fondling Pennywise again," Jack says, waving a hand towards the party going on inside.

Will had almost forgotten about that, so wrapped up in the moment. He turns to the doors, one hand on his hip as he nods, "Well, it looks like she may have mistaken Grace's bright red lipstick and garish choice of hairstyle for him."

"Oh, yeah," Jack tilts his head to the side, nodding as he watches as Grace bats away a handsy, drunk Karen. "Well, that's nothing new."

Will laughs as he follows Jack back inside, the weight of what could have been still hanging in the air.

\- - -

Will tries everything.

Fancy dinners at restaurants, movies sat in the back row with their knees touching, theatre tickets to Jack's favourite shows, late night walks through Central Park, coffee and long chats on benches.

No matter what, when it comes down to it, he still can't get the words out. A grand gesture isn't enough to get him to say them. Not even Jack's kindness, or Jack's biting remarks about other people that leave Will's ribs aching with laughter, or Jack's coy smile when he wrangles money out of Will who can't refuse to say no, can get Will to confess.

He's starting to think that maybe it isn't to be. He's haemorrhaging money by coming up with these elaborate _dates-but-not-dates_ to tell Jack how he feels and it's leading nowhere.

Will's starting to get sick with jealousy whenever Jack dates someone new, and in Jack's world, that's every other week.

It's been months. Valentine's Day, Thanksgiving, Christmas. All perfect opportunities to tell Jack how he feels and all of them wasted.

He's given up. He can't do this to himself anymore. He has to stop feeling this or hurry up and come out with it.

He decides to go with the former, goes on dates and even speaks to Vince, but nothing works. He can't just turn off the feelings like a light switch.

He's still in love with Jack. _Sweet, cocky, vain, funny, caring Jack. Will always be there for him and loves him Jack._

Will supposes he's going to have to suck it up and die feeling this way.

Afterall, if watching _Call Me By Your Name_ with Jack can't muster up the strength he needs to confess, then what can?

\- - -

Jack is hungover, sitting at Will's breakfast table and eating from a bowl of granola, groaning at every other bite due to the pain that shoots through his head.

Will watches him between sips of coffee. It's a sight he's seen time and time again, to the point where it's almost monotonous, Jack straying from his own apartment to Will's, no doubt because he hasn't bought any food that week and instead spent his money on something ridiculous, like a cushion with Ryan Gosling's face on it. (One that Will no doubt will borrow and claim it's because it helps with lumber support.)

Despite his pounding head, Jack is recalling his night with a pleased smile on his features, telling Will about how he managed to get three numbers and how he hit on the DJ before realising they were a rather androgynous lesbian, so now he has a lesbian friend, _'which, as you know, is new for me.'_

Will doesn't cut in on Jack's words, just listens and chuckles, hanging onto the nonsensical storytelling on an almost fourty-nine year old, enthusiastic gay man who hasn't changed since the moment Will met him.

It's only when Jack trails off from another tangent to take a long gulp of orange juice, does Will cut in, sighing as he speaks, the words rolling out like it's natural, "I'm in love with you, Jack."

Jack swallows hard, almost choking on his juice as his eyes widen over the brim. He slams the cup back onto the table, the sound of it alerting Will, whose own eyes widen as he slowly realises what he's done. 

Jack's heart thrums in his ears as he stares at Will, watches the slow panic creeping across the other man's features. Jack reaches his hands out, stops Will from fleeing as the two of them rise to their feet, hand curling around Will's wrist, "Wait, Will, stop!"

Will blinks at him, slow and reluctant, stomach twisting in knots.

Jack rubs a thumb across Will's knuckles, an anchor that soothes Will as he swallows, throat dry. _He's screwed up, hasn't he?_

Jack's lips stretch into a smile, blue eyes soft and brimming with something that Will can't quite analyse, as he awaits Jack's response. Letting out a soft chuckle, Jack's eyes drift to the hand that joins the two of them, palm splaying open to twine their fingers together, squeezing gently. 

Before Will can comprehend what's happening, there's the warmth of fingertips pressed to his cheek and Jack is leaning forward, lips sliding against his own in a soft touch. 

Will blinks, taking in the shift of their positions, and then his lashes are closing and his lips are moving against Jack's, a tender touch that he's been pining for for months. Hands moving to Jack's arms, he pulls him closer, their noses bumping together lightly as they both sink into the warmth of the kiss.

It feels like a lifetime before they pull apart, foreheads pressing together as the fingers on Jack's free hand curl around the nape of Will's neck, brushing at the soft hair there as Will strokes his thumbs across Jack's biceps.

"You have no idea how long I've been waiting to hear you say that," Jack whispers, lips curled into a warm smile, chest giddy as tears prick behind his eyelids.

Will's a mirror image, laughing softly, nose brushing against Jack's as he leans against him. He really had no idea. Despite the hints Jack would drop and the jokes he would make over the years, Will had always just put it down to Jack's vanity and him thinking everyone was in love with him. Hell, he'd even confessed years ago to liking him, and Will had rejected him. Sure, they were both young, but... _he should have known._

"You gonna say it back?" Will opens his eyes, pulling back as he looks up at Jack, who opens his own eyes and smiles at him.

"Hmm," Jack considers, a smirk on his features. "We may need to make out a little first. Make sure I really know."

Will chuckles, rolling his eyes at Jack's idea of teasing. He leans in again, fingers sliding down Jack's arm towards his hip, pulling him close until their bodies are aligned, hips pressed together. 

Jack's chuckle is caught in his throat, eyes widening as Will's warm breath hits his cheek.

"I'm sure I can get it out of you eventually," Will grins before closing the gap between them.

**Author's Note:**

> i've shipped this since i was fourteen and almost ten years later, i'm still the same, rip.
> 
> i hope i got the tone of the show down ok.


End file.
